Anna Maria Island

I’m lucky to have some incredible options for a staycation in Florida. This year we wanted to play it safe, but we also wanted to have a small getaway with our family, so we stayed close and rented a house in Anna Maria Island.

Hands down, Anna Maria Island is my favorite beaches of all time. The sand is soft, powdery and white while the waters around the small island are crystal clear and brilliant blue. Anna Maria Island is only a two hour dive from where we live in Orlando, but for some reason I’d never been there during the 18 years I’ve lived in Florida.

Anna Maria a sleepy little beach town that reminded me a little bit of my hometown in Winter Garden, without the big hotels and crowds found along much of the Florida coast. There isn’t a whole lot to do here, and that is sort of the charm of it all. People visiting the island get around the island by golf cart, fish from one of the two piers, bike down to Pine Street in their flip flops for an ice cream cone at Dipps or make your own doughnuts at The Doughnut Experiment.


This trip we brought our groceries from home, didn’t go out to eat, and made all meals at our rental house. Long sunny days were spent in the warm sand of the beach, most evenings we watch led beautiful sunsets, and one evening everyone walked down for an ice cream treat outside.

Maxwell mastered paddle boarding this trip!

Each afternoon a tidal pool slowly formed for the little ones to splash around. The older kids swam, snorkeled, and Max learned how to use my stand up paddle board (SUP) all by himself. Every morning, Maxwell would sit on the front of my SUP and I paddled us up to the end of Bean Point and back. On one of our trips on the SUP, several humongous stingrays glided right under us on the board, like that scene from Moana! We also spotted several manatee right off the beach that were close enough to touch (though we didn’t, because that’s a no-no).

There was a giant lightning strike right as I took this photo, but I think it makes it even better.

Since we knew we weren’t going out this trip, I made sure to look for a house that had a good dining and living area that was big enough for the kids dance parties at night. The house we rented included an elevator for older family members. The pool was partially under the back porch so the kids could get out of the sun for a bit.

Anna Maria Island was a wonderful place for a socially distant vacation this summer, and just what our family needed. Now that I’ve discovered this gem, I think I’ll be coming back every year.

Max and his cousin Elliott en route to ice cream.
My pretty niece Camryn.
Emerald waters at Bean Point
All tuckered our after days at the beach.
Maxwell walking with his PapPap.

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